US4958020AExpiredUtility

Process for producing β-lactamase inhibitor

Assignee: AMERICAN CYANAMID COPriority: May 12, 1989Filed: May 12, 1989Granted: Sep 18, 1990

Est. expiryMay 12, 2009(expired)· nominal 20-yr term from priority

Inventors:Raghavan Krishnan Jesse Gamble David Blum William V. Curran Ving J. Lee Ransom B. Conrow

C07D 499/00A61P 31/04C07D 499/86

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Abstract

A process for producing the compound [2S-(2α,3β,5α)]-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3 2 0]-heptane-2-carboxylic acid, (4-nitrophenyl)methyl ester, 4,4-dioxide, which comprises reacting a solution of azidopenamsulfone, 4-methoxyphenol and vinylpropionate with a solution of bis(trimethylsilyl)acetamide and 4-methoxyphenol is toluene at 80°-100° C. for 18-30 hours followed by filtering the resulting solution and cooling the filtrate to 0°-10° C.

Claims

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We claim: 
     
       1. A process for producing the compound [2S-(2α,3β,5α)]-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid, (4-nitrophenyl)methyl ester, 4,4-dioxide, which comprises reacting a solution of azidopenamsulfone, 4-methoxyphenol and vinylpropionate with a solution of bis(trimethylsilyl)acetamide and 4-methoxyphenol in toluene at 80°-100° C. for 18-30 hours followed by filtering the resulting solution and cooling the filtrate to 0°-10° C.

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